Formose reaction controlled by boronic acid compounds

• Toru Imai,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2668–2672, doi:10.3762/bjoc.12.263

• boronic acid esters. On the other hand, the 1H and 13C NMR spectra for pVPB/NaSS show well-resolved signals, indicating that the formose reaction provides products with a significant selectivity in the presence of pVPB/NaSS. Figure 4 displays typical examples of electrospray ionization mass spectrometry

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

• Constantin Mamat,
• Marc Pretze,
• Matthew Gott and
• Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

• 13C spectra were reported in parts per million (ppm) using TMS as internal standard for 1H/13C and CFCl3 for 19F spectra. Mass spectrometric (MS) data were obtained on a Xevo TQ-S mass spectrometer (Waters) by electron spray ionization (ESI). The melting points were determined on a Galen III melting

A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane

• Donghui Pan,
• Yanbin Wang and
• Guomin Xiao

Beilstein J. Org. Chem. 2016, 12, 2443–2449, doi:10.3762/bjoc.12.237

• points were determined using a Beijing TaiKe X-4 melting point apparatus and were uncorrected. Mass spectra were obtained using an Agilent 1260-6224 spectrometer with electron impact ionization (EI, 70 eV). Elemental analyses were recorded on an Elementar vario MICRO cube. Typical reaction procedure for

Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides

• Ilya V. Efimov,
• Marsel Z. Shafikov,
• Nikolai A. Beliaev,
• Natalia N. Volkova,
• Tetyana V. Beryozkina,
• Wim Dehaen,
• Zhijin Fan,
• Viktoria V. Grishko,
• Gert Lubec,
• Pavel A. Slepukhin and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2016, 12, 2390–2401, doi:10.3762/bjoc.12.233

• 1H and 13C NMR spectra were recorded on Bruker Avance II spectrometer in DMSO-d6 or CDCl3 (400 and 100 MHz, respectively) using Me4Si as an internal standard. Mass experiments were performed on Shimadzu GCMS-QP2010 Ultra gas chromatograph operating at an ionization potential of 70 eV (EI). The IR

Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

• Manuela Oliverio,
• Paola Costanzo,
• Monica Nardi,
• Carla Calandruccio,
• Raffaele Salerno and
• Antonio Procopio

Beilstein J. Org. Chem. 2016, 12, 2222–2233, doi:10.3762/bjoc.12.214

• , then returning to 5% in 1 minute. At the end it was re-equilibrated for 3 minutes. The total run time, including column wash and equilibration was 15 min. A Thermo Scientific Q-ExactiveTM mass spectrometer was used for HRMS measurements using electrospray as ionization source with both negative and

Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element

• Reji Thomas and
• Nobuyuki Tamaoki

Beilstein J. Org. Chem. 2016, 12, 2211–2215, doi:10.3762/bjoc.12.212

• ionization time-of-flight mass spectrometry (MALDI–TOFMS) was performed with an Applied Biosystems Voyager-DE pro instrument. Absorption spectra were recorded with an Agilent 8453 spectrophotometer and the CD spectra were recorded with a JASCO J-S720 CD spectrophotometer. High-performance liquid

Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

• Xiaofeng Zhang,
• Kenny Pham,
• Shuai Liu,
• Marc Legris,
• Alex Muthengi,
• Jerry P. Jasinski and
• Wei Zhang

Beilstein J. Org. Chem. 2016, 12, 2204–2210, doi:10.3762/bjoc.12.211

• 365 nm. Low resolution mass spectra were recorded with APCI (atmospheric pressure chemical ionization). The final products were purified on Angela HP-100 pre-LC system with a Venusil PrepG C18 column (10 μm, 120 Å, 21.2 mm × 250 mm). General procedure for the one-pot synthesis of compounds 7 The

Solvent-free synthesis of novel para-menthane-3,8-diol ester derivatives from citronellal using a polymer-supported scandium triflate catalyst

• Lubabalo Mafu,
• Ben Zeelie and
• Paul Watts

Beilstein J. Org. Chem. 2016, 12, 2046–2054, doi:10.3762/bjoc.12.193

• a flame ionization detector, Econocap-5 column (film thickness 0.25 µm; internal diameter 0.25 mm; length 30 m) and ultra-high purity nitrogen (99.999%) carrier gas. The samples were analysed by using the following method; injector temperature 270 °C, nitrogen flow rate 0.5 mL·min−1, oven

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• notion of taking some cells, putting in nanoparticles, and then throwing them in the matrix-assisted laser desorption ionization (MALDI) mass spectrometer without matrix. Quite surprisingly, all the student could see was the ligand on the particle – with essentially no signal from all of the rest of the

• stuff found in cells [68]. This was the start of a collaboration that continues to this day, where we have used laser desorption ionization (LDI) to characterize ligands on particles [69][70], supramolecular chemistry in cells [71], track NPs in fish [72] and plants [73], and to image NPs in animal

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• Spectrometry Service Facility of the Organic-Chemical Department of the University of Heidelberg using the following instruments: Vacuum Generators ZAB-2F, Finnigan MAT TSQ 700, JEOL JMS-700, Bruker ICR Apex-Qe hybrid 9.4 T FT-ICR. In general the ionization method was specified. Apart from the method of

• ionization and the peak of the molecular ion, the base peak and characteristic fragmentation peaks with their relative intensities are reported. Syntheses 3,3'-(Ethane-1,2-diyl)bis(4,5-dimethylthiazolium) dibromide (1a) A Schlenk flask was charged with 3.00 equiv 4,5-dimethylthiazole (1.00 g, 8.84 mmol) and

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• photoabsorption properties. Experimental General methods Matrix-assisted laser desorption ionization time-of-flight (MALDI–TOF) mass spectra were collected on a Bruker Daltonics Autoflex III spectrometer using dithranol as the matrix. Elemental analysis was carried out using a YANACO CHN coder MT-6

Reactivity studies of pincer bis-protic N-heterocyclic carbene complexes of platinum and palladium under basic conditions

• David C. Marelius,
• Curtis E. Moore,
• Arnold L. Rheingold and
• Douglas B. Grotjahn

Beilstein J. Org. Chem. 2016, 12, 1334–1339, doi:10.3762/bjoc.12.126

• and of the C–H bond of acetylene. The same ligand in CpRu complexes 2 and 3 showed heterolysis of dihydrogen [13]. 1 had a much faster ligand exchange rate after ionization as compared to the Cp*Ir analog (ethylene bound in 5 min at rt (CpRu) instead of 16 h at 70 °C (Cp*Ir)). Species 1 could be

On the mechanism of imine elimination from Fischer tungsten carbene complexes

• Philipp Veit,
• Christoph Förster and
• Katja Heinze

Beilstein J. Org. Chem. 2016, 12, 1322–1333, doi:10.3762/bjoc.12.125

• mechanistic studies to the formation of imine E-3 are performed by NMR, IR and UV–vis spectroscopy and liquid injection field desorption ionization (LIFDI) mass spectrometry as well as by trapping experiments for low-coordinate tungsten complexes with triphenylphosphane. W(CO)5(E-2) decays thermally in a

Artificial Diels–Alderase based on the transmembrane protein FhuA

• Hassan Osseili,
• Daniel F. Sauer,
• Klaus Beckerle,
• Marcus Arlt,
• Tomoki Himiyama,
• Tino Polen,
• Akira Onoda,
• Ulrich Schwaneberg,
• Takashi Hayashi and
• Jun Okuda

Beilstein J. Org. Chem. 2016, 12, 1314–1321, doi:10.3762/bjoc.12.124

• (polyethylene-polyethylene glycol), SDS (sodium dodecyl sulfate), TEV (Tobacco Etch Virus), MALDI–TOF–MS (matrix-assisted laser desorption/ionisation and time-of-flight mass spectrometry), FhuAΔCVFtev (FhuA Δ1-159_C545_V548_F501_tev), CD (circular dichroism), ESI-MS (electrospray ionization-mass spectrometry

Nucleic acids through condensation of nucleosides and phosphorous acid in the presence of sulfur

• Tuomas Lönnberg

Beilstein J. Org. Chem. 2016, 12, 670–673, doi:10.3762/bjoc.12.67

• ionization mass spectrometric (ESIMS) analysis of the collected fractions suggested the main products to be short oligonucleotides with internucleosidic phosphorothioate linkages. As could be expected, retention times in the IE HPLC correlated with the number of the negatively charged phosphorus-containing

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• theoretical values for a monosubstituted rhodamine-β-CD derivative. This is also confirmed by the found value of the pseudo-molecular ion during the electrospray ionization mass spectrometry (ESIMS) analysis (see Experimental part). The resonance signals in the aromatic region are well resolved (see

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• identified as piericidin derivatives (e.g., piericidin A1 (1), Figure 3) and the chlorinated indole derivative streptochlorin (2). Imaging analysis based on a combination of laser desorption/ionization (LDI)–time of flight (TOF) mass spectrometry imaging visualized the spatial distribution of the antibiotics

Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions

• Jixin Liu,
• Srimoyee Dasgupta and
• Mary P. Watson

Beilstein J. Org. Chem. 2015, 11, 2696–2706, doi:10.3762/bjoc.11.290

• alkynylations in good yields and ee’s. In 2011, we reported the first example of enantioselective alkynylation of a cyclic oxocarbenium ion intermediate (Scheme 15) [55]. Isochroman oxocarbenium ion 41 was formed in situ via Lewis acid-mediated ionization of a racemic acetal precursor. By using a Cu(MeCN)4PF6

Synthesis of cyclic N¹-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

• Ahmed Mahal,
• Stefano D’Errico,
• Nicola Borbone,
• Brunella Pinto,
• Agnese Secondo,
• Valeria Costantino,
• Valentina Tedeschi,
• Giorgia Oliviero,
• Vincenzo Piccialli and
• Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

• on a Bruker APEX II FT-ICR mass spectrometer using the electrospray ionization (ESI) technique. Column chromatography was carried out on silica gel-60 (Merck, 0.063–0.200 mm) or on C-18 reversed-phase silica gel-60 (Merck, 0.040–0.063 mm). Analytical TLC analyses were performed using F254 silica gel

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• emitting materials owing to their pure blue emission [7][8][9][10][11]. However, some major drawbacks for their use are their high ionization potential associated with low photoluminescence (PL) efficiency, their rather large band gap and facile photochemical degradation [12][13]. Different strategies have

• macromolecular chains and the macrocycles, 3, 3·TM-βCD and 3·TM-γCD were electrochemically investigated by cyclic voltammetry (CV), Figure 4 and the results are summarized in Table 2. The Ep,onset and En,onset values allow the estimation of the ionization potential (IP), electron affinity (EA) and energy band

Iron complexes of tetramine ligands catalyse allylic hydroxyamination via a nitroso–ene mechanism

• David Porter,
• Belinda M.-L. Poon and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 2549–2556, doi:10.3762/bjoc.11.275

• chromatographs were equipped with split/splitless capillary inlets and flame ionization detectors (FID). UV–vis spectra were recorded on a Varian Carey 4000 UV–vis spectrophotometer. Synthesis of iron complexes 4, 5 and 6 and N-Boc-hydroxylamine (8) Tris(2-pyridylmethyl)amine (TPA, 1) [48] and N,N′-bis(2

Comparison of the catalytic activity for the Suzuki–Miyaura reaction of (η⁵-Cp)Pd(IPr)Cl with (η³-cinnamyl)Pd(IPr)(Cl) and (η³-1-t-Bu-indenyl)Pd(IPr)(Cl)

• Patrick R. Melvin,
• Nilay Hazari,
• Hannah M. C. Lant,
• Ian L. Peczak and
• Hemali P. Shah

Beilstein J. Org. Chem. 2015, 11, 2476–2486, doi:10.3762/bjoc.11.269

• (GC) were performed on a Shimadzu GC-2010 Plus apparatus equipped with a flame ionization detector and a Shimadzu SHRXI-5MS column (30 m, 250 μm inner diameter, film: 0.25 μm). The following conditions were utilized for GC analyses: flow rate 1.23 mL/min constant flow, column temperature 50 °C (held

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• chemical shift value, 400 MHz is reported as δ using the residual solvent signal as internal standard at ≈22 °C. Mass spectrometry Mass analysis was done using matrix-assisted laser desorption ionization (MALDI) on a Waters Synapt G1 using 2,5-dihydroxybenzoic acid as the matrix. Microcalorimetric

Convenient preparation of high molecular weight poly(dimethylsiloxane) using thermally latent NHC-catalysis: a structure-activity correlation

• Stefan Naumann,
• Johannes Klein,
• Dongren Wang and
• Michael R. Buchmeiser

Beilstein J. Org. Chem. 2015, 11, 2261–2266, doi:10.3762/bjoc.11.246

• up, ranging from 200 000 g/mol to over 400 000 g/mol (Mn). Importantly, in all these cases very high conversion is observed. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI–ToF MS) and NMR experiments clearly show that BnOH is incorporated in the resulting PDMS (S1